Piperidine → HCID 59375150, compound

HRID 1811122Notes

Reaction equation

HRID 1811122 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([NH:8][C:9]2[C:10]([CH3:33])=[C:11]([C:15]3[C:27]4[C:26]5[C:21](=[CH:22][C:23]([CH:28]=O)=[CH:24][CH:25]=5)[NH:20][C:19]=4[C:18]([C:30]([NH2:32])=[O:31])=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]([CH3:33])=[C:11]([C:15]3[C:27]4[C:26]5[C:21](=[CH:22][C:23]([CH2:28][N:36]6[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]6)=[CH:24][CH:25]=5)[NH:20][C:19]=4[C:18]([C:30]([NH2:32])=[O:31])=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 8082Piperidine2×HCID 5049666Sodium triacetoxyborohydride2×HCID 86642952HCID 86642952, compound

Product 1

HCID 59375150HCID 59375150, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A suspension of 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-formyl-9H-carbazole-1-carboxamide (30 mg, 0.064 mmol) in THF (3 mL) was treated with piperidine (16.46 mg, 0.193 mmol) and sodium triacetoxyborohydride (34.1 mg, 0.161 mmol). The mixture was stirred at rt for 3.5 h, the was treated again with additional piperidine (16.5 mg, 0.193 mmol) and sodium triacetoxyborohydride (20 mg). After stirring overnight, the mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was purified by preparative HPLC to provide 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(piperidin-1-ylmethyl)-9H-carbazole-1-carboxamide (14 mg, 39%). 1H NMR (400 MHz, methanol-d4) δ 8.06 (2 H, dd, J=8.7, 5.4 Hz), 7.98 (1 H, d, J=7.8 Hz), 7.63 (1 H, s), 7.52 (1 H, d, J=7.3 Hz), 7.44 (1 H, t, J=7.8 Hz), 7.18-7.31 (3 H, m), 7.07 (2 H, d, J=7.5 Hz), 6.96-7.02 (1 H, m), 3.96 (2 H, s), 2.72-2.88 (4 H, m), 1.99 (3 H, s), 1.63-1.75 (4 H, m), 1.48-1.60 (2 H, m). Mass spectrum m/z 535.2 (M+H)+.

Workup

  1. stirringAfter stirring overnight
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b51b8b862a7d4b6e959c3057c5b7b1ad
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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